13 Lasting Business Lessons I Learned From Delivering Pizza


The robots are now delivering pizza, stealing the jobs from acne-cratered 19 year olds in every college town.

Dominos just announced that self-driving robots will deliver pizzas. This is the new world.

So, as the last generation to physically have a delivery job I feel it’s my responsibility to share the life lessons I learned delivering pizza.

Pay attention!

1. Be on Time

It’s so easy to keep a customer happy. If you order a pizza, it means you’re probably hungry right then.

My only job is to stuff your face with cheese and bread as quickly as possible. If I do that, I get paid, and I win you over for life.

If I don’t do it, no tip, and no repeat customer. Being on time for everything is the most important thing and it’s so easy to do.

2. Don’t Tilt the Pizza

In every business I’ve ever been involved in, the problems are never the big catastrophes.

A big catastrophe is exactly when founders, CEOs, and investors, get to show their skills and perform their best to solve the problem.

But it’s the wear and tear of mediocrity at every level of a team that will bring about downfall.

I would tilt the pizza. I was a “tilter” as we call it in the biz.

And all the cheese would fall to the side. I was that guy! People would hate me. It’s never good when the people who want to love you, actually hate you.

Make a checklist of the basics: be on time, don’t tilt, know the address where you are doing, and make sure the order is correct.

Don’t forget a coke or you can end up having to go back and forth to get a single coke.

3. Read a Book

Some of the best moments of my life were this:

After delivering a pizza, and with no new orders, I’d find some place to park and I’d take out a book and read.

No matter what job I’ve been in ever since, I’ve always prized the moments of alone time to both rejuvenate and learn.

Plus I had a girlfriend I was trying to avoid.

4. Evil Plan

I was delivering pizza because I started a pizza (and other food) delivery business. We delivered from about eight different restaurants in a college town.

And the reason we set up a delivery business is because we set up a debit card business. So to every restaurant that accepted our debit card, we offered the ability to deliver to our debit card customers.

Sometimes a delivery job is just that, a delivery job.

But I always want to see how I can leverage what I’m doing into something else, and then leverage that something else into something else.

What got me out of bed in the morning was not the thought that, “today I get to deliver pizza” but the thought that, “my evil plans are getting closer to world domination!”

Even now, if I don’t have that evil plan, I have trouble getting up in the morning.

5. Deliver a Round Pizza

This advice comes from a friend of mine. He ran 20 Dominos franchises. He bought them in South Florida when they were failing.

He then turned them around, sold them, and made millions.

I asked him, “How could a Dominos franchise fail?” which may seem like a stupid question. Every business can fail. But a franchise is usually pretty well regimented.

He said, “I got there, and the pizzas weren’t round. They were misshapen. They were like trapezoids.

Just deliver a pizza in the correct shape and people will keep ordering. Instead, they got a reputation for sloppiness.”

I think of this now with podcasting. I started off doing podcasts over three years ago thinking that audio quality didn’t matter so much. “It’s just the Internet!” I said.

But now I use a professional studio for each podcast (costs as low as $70 / hr) and I try to meet each guest in person so the quality is the highest it can possibly be for relatively little cost.

Even when other people have me on their podcasts, I often will set it up in a studio to make sure its high quality.

6. If it’s Not Growing, it’s Dead

We ran that delivery business for a year. But the orders in the last month were the same as the orders in the first month.

Maybe we could have fixed it but we just didn’t have the skills to do so.

Every happy chemical in the brain (serotonin, dopamine, oxytocin) likes it when you are increasing competence, increasing relationships, increasing freedom.

Children are made to explore and be curious. They don’t think about purpose. They think about “why?”

But we forget that.

It’s easy to stop things when a business or relationship fails. It’s also easy to continue when things are going well.

But it’s hard to know what to do when things seem to have flatlined.

My rule now is: if things are flatlining for 90 days and, to my best efforts, I can’t get things to improve or at least have hope for improvement, then I shut it down.

An example is my recent podcast, “Question of the Day” I was doing with Stephen Dubner.

It was a quality podcast and we were getting about 700,000 downloads per month. It wasn’t doing bad. It was just sort of staying the same.

We lost energy for it. We were getting advertisers and money each month but it lost that excitement of a child having fun and exploring and growing.

So we stopped. Stephen now is doing the excellent podcast “Tell Me Something I Don’t Know” (in addition to “Freakonomics Radio”) and the downloads on my own show have doubled or tripled.

I try now to always double-down on what is growing and stop the flatlining.

7. It’s a Pleasure to Serve You

I like being in the service business. I liked delivering pizza.

40,000 years ago people would have to hunt down a bull, slice it up into tiny pieces, milk a female cow and spoil the milk into cheese, harvest wheat, make a fire, get sugar from somewhere and put it into a carbonated drink (and I have NO IDEA how they invented those).

Then they’d have to go to a group of islands off the coast of Indonesia to get some spices and bring it back.

And then they would be able to eat a pizza.

Then…40,000 years later…they could call me on a phone and 10 minutes later I’d come in the door and make them happy.

Evolutionary kind of Happy! I had just solved all of these major problems that took humans 40,000 years to solve.

I ran an agency business in the 90s. Like any agency, rule #1 is, use your client’s products. Love your clients. Why serve people you don’t like. We only get one life to be with the people we love.

The same thing for delivery. If they were having a party, and ordering 10 pizzas, then I was happy to help make their party better. It made my life better, my enthusiasm translated to tips, and it made their lives better.

8. Dress for the Job You Want

Wende also delivered pizzas with me. She was a co-founder in the business as well. Her dad was a billionaire but she delivered faster than me and got better tips.

Also, she was blonde and beautiful. So, I hate to say it, guys liked to give her better tips than they gave me.

When I would clean up and wear a button down white shirt and black pants (like a waiter), I would get better tips. It was that simple.

I still wear a white button down shirt and black pants. I still get better tips.

9. The 360 Degree Rule

The reason the Dominos pizza franchises failed, above, is because they didn’t deliver a round pizza and didn’t deliver when they said they would.

Somehow, they never learned the entire premise and history of how Dominos started. They probably assumed a pizza delivery business right next to a major college was a home run no matter what.

It’s not.

Learn the history of the business and the history of the founder. Learn how to make the pizza. Learn about the service industry and who succeeded and who failed.

For my business, I was the sales person who convinced each restaurant to let us deliver for them.

I also was the programmer who programmed the point of sales machines to accept the debit cards we created.

I also sold advertising on the back of the debit cards, something I still have not seen ever since on the backs of credit cards (you’re very welcome Q104 Radio in Ithaca, New York).

When I started at HBO, I learned the history of how satellites transformed television delivery. I learned how the then-executives of HBO sold door to door against Showtime 20 years earlier when they were junior sales people.

I studied how Time Warner was structured and how the companies worked together. So, later, I was able to network and do jobs for Warner Brothers, People Magazine, Comedy Central, New Line Cinema, TNT, and even do the website for TImeWarner.com.

It’s grow or die. In other jobs I’ve had, I didn’t do this. I was the tenth employee of Fore Systems, a company that eventually sold for around three billion.

But all I did was get in late for work, close the door to my office, barely did my job, and left early.

So eventually I left and didn’t get wealthy in my 20s like everyone else did who started there with me.

Does this apply to every pizza guy? Or every newspaper delivery guy? Or every cashier?

Yes it does. Grow or die.

Learn all 360 degrees of every job you have, no matter how low. That knowledge will compound over the years even if it seems trivial or unimportant when you learn it.

10. Don’t Talk Bad about your Bosses or Partners

My first year of college I got very bad grades. My dad came up to visit me to find out what was going on.

I had to hide the fact that I was living with my girlfriend (my parents paid no money for my college or living expenses), so I always said, “let’s just walk around. I’ll show you the campus.”

While we were walking around I kept trashing the people I was working with, my partners in the business.

He stopped me at one point and just said, “Don’t do that. It’s not good.”

I had to think about it. He was worried somehow they would hear what I was saying.

But also he felt I should figure out how to work better with them instead of complain. So I did.

And he was right. And it helped make every decision better and now I have the fondest memories of this time in my life.

And of my dad, who is dead.

11. 80/20 Rule

There were about four good pizza places in town. We delivered from the best. And from the best Greek place. And the best Middle-Eastern place.

But here’s what I wish we did. I wish we had created one menu with just the best items from each place. It’s the 80/20 rule. 80% of the people ordered less than 20% of the items on all of the menus.

We could have streamlined the business quite a bit and maybe even have grown faster if we had simply offered only the most popular items and all on one menu. Then we could’ve marketed our delivery services better.

12. Use it or Lose it

I had no money and my grades were so bad I was at risk of getting thrown out of college. So I had to not only work 40 hours a week or more, but pay more attention to my classes.

And I hated classes. HATED them. I would skip midterms and fail homework.

One thing I found out, which I never knew before at my tender age, is that the more hours I worked at delivery and my business, the better my grades got.

I couldn’t figure out why. I guess I still don’t know why. The only thing I can figure is that the more discipline I built up in one area of my life, the more discipline would build up in ALL areas of my life.

When I had a lot of free time, I’d obsess on relationships, and emotional drama, and try to maximize my free time instead of trying to be as productive as possible in my work time.

Now when I have free time I do “dual-use” free time. I do things I enjoy, but I make sure they carry over to other areas of my life.

For instance, I have free time right now. So I read an article about how robots are delivering pizza. And it brought back late night memories of delivering at 2 in the morning to fraternity parties.

So with my free time I write this article. And now I love that I delivered pizza 30 years ago to the day.

13. Fred

Fred was a linebacker on the football team – which means he was probably the worst linebacker in college football history.

He also was a decent chess player. So I hired him to deliver with us when things were busy.

We’d sit by the phone waiting for an order and play speed chess until 5 in the morning.

One time when I was in between deliveries I went over Fred’s place and he climbed out of bed and he found a scrunched up board and clock and we played blitz on the floor.

His bed was covered with clothes and his apartment was a mess. In the middle of the game, this naked girl rises up from the mess in the clothes on the bed.

She was beautiful and i fell in love with her. I couldn’t stop staring.

Fred kept staring at the chessboard. “Look away,” he said to me, but I couldn’t.

“Put your eyes back on the board,” he said but I couldn’t.

“Fred, what are you doing!”

“Don’t worry, baby, you’re just dreaming,” Fred said.

“Who is this guy?”

“Don’t worry.”

But I couldn’t focus anymore. Fred won the game and I went back to delivery.

I worked hard at that business and it didn’t work out but I can’t say it failed.

It’s a memory for me. Brought to life this morning by robots from Dominos.

I had created something out of nothing for the first time in my life. I hated it, I learned, I lived it. I wish I had enjoyed it a bit more.

The Terminator is not coming to kill us. It’s coming to deliver us a pizza with everything.